4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[3,5-O-(di-tert-butylsilylene)-2-O-triisopropylsilyl-α-D-arabinofuranosyl]-α-D-arabinofuranoside | 1621691-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-2-O-[3,5-O-(di-tert-butylsilylene)-2-O-triisopropylsilyl-α-D-arabinofuranosyl]-α-D-arabinofuranoside
• CAS: 1621691-88-0
• 化学式: C₄₉H₆₉ClO₁₂Si₂
• 分子量: 941.704
• InChiKey: ICFADGSLPKNDDE-CSVKBEGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.62
• 重原子数：
  64.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  126.44
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  phenyl 3,5-di-O-(di-tert-butylsilylene)-2-O-triisopropylsilyl-1-thio-α-D-arabinofuranoside 、 4-(2-chloroethoxy)phenyl 3,5-di-O-benzoyl-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以63.636%的产率得到
  参考文献：
  名称：

  The use of O-trifluoroacetyl protection and profound influence of the nature of glycosyl acceptor in benzyl-free arabinofuranosylation

  摘要：

  The influence of O-trifluoroacetyl (TFA) groups at different positions of thioglycoside glycosyl donors on stereoselectivity of α-arabinofuranosylation leading to corresponding disaccharides was studied. It was shown that TFA group in thioglycoside glycosyl donors, when combined with 2-O-(triisopropylsilyl) (TIPS) non-participating group, may be regarded as an electron-withdrawing protecting group that may enhance 1,2-cis-selectivity in arabinofuranosylation, the results strongly depending on the nature of glycosyl acceptor. The reactivities of the glycosyl donors were compared with those of a similar thioglycoside with O-pentafluoropropionyl groups and the known phenyl 3,5-O-(di-tert-butylsilylene)-1-thio-α-d-arabinofuranosides with 2-O-TIPS and 2-O-benzyl groups. The 'matching' in the donor-acceptor combination was found to be critical for achieving both high reactivity of glycosyl donor and β-stereoselectivity of arabinofuranosylation. The use of glycosyl donors with TFA and silyl protection may be useful in the realization of the benzyl-free approach to oligoarabinofuranosides with azido group in aglycon-convenient building blocks for the preparation of neoglycoconjugates.

  DOI：

  10.1016/j.carres.2014.05.017